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Chemical Structure| 1271-51-8
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Product Details of [ 1271-51-8 ]

CAS No. :1271-51-8 MDL No. :MFCD00001434
Formula : C12H12Fe Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 212.07 Pubchem ID :-
Synonyms :

Safety of [ 1271-51-8 ]

Signal Word:Danger Class:4.1
Precautionary Statements:P210 UN#:1325
Hazard Statements:H228 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1271-51-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1271-51-8 ]

[ 1271-51-8 ] Synthesis Path-Downstream   1~85

  • 2
  • [ 12093-10-6 ]
  • [ 1779-49-3 ]
  • [ 1271-51-8 ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; pentane at 0℃; for 0.333333h; Stage #2: ferrocenecarboxaldehyde In tetrahydrofuran; pentane at 20℃;
90.9% With n-butyllithium In tetrahydrofuran under N2; soln. of ferrocene deriv. in THF added to soln. of MePh3PBr and n-BuLi in THF/hexanes at 0°C, mixt. stirred for 24 h; water added, org. layer sepd. and evapd. to dryness, column chromy. (silica gel, hexane/ethyl acetate (4/1)); elem. anal.;
89% With phenyllithium In tetrahydrofuran N2-atmosphere; stirring of phosphonium salt and PhLi (1 h, 22-27°C), addn. of formylferrocene (during 20 min), stirring (1 h, 22-27°C); addn. of petroleum ether, filtration, solvent removal (reduced pressure), chromy. (Al2O3, Et2O/petroleum ether=2:1), evapn. (reduced pressure), drying (vac.);
85% Stage #1: Methyltriphenylphosphonium bromide With lithium tert-butoxide In tetrahydrofuran for 0.25h; Schlenk technique; Stage #2: ferrocenecarboxaldehyde In tetrahydrofuran at 20℃; Schlenk technique;
81% Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere; Stage #2: ferrocenecarboxaldehyde In tetrahydrofuran at 23℃; for 18h; Inert atmosphere;
70% Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: ferrocenecarboxaldehyde In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;
65% Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: ferrocenecarboxaldehyde In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; 3.2. General procedure for Wittig reaction (procedure A) General procedure: To a suspension of methyltriphenylphosphonium bromide (1equiv.) in dry THF (100 mL), under nitrogen atmosphere at room temperaturewas added potassium tert-butoxide (7.0 equiv.). The solutionwas stirred for 1 h and then a solution of the aldehyde (1 equiv.) indry THF (30 mL) was added slowly. The mixture was stirred at roomtemperature for 12 h andwas evaporated to dryness. The unreacted potassiumtert-butoxide was quenched with saturated NH4Cl solution(10 mL). The reaction mixture was then extracted with CHCl3(200 mL), washed with water (2 × 200 mL), brine (100 mL) and then dried over anhydrous Na2SO4. Evaporation of the organic layer gave aresidue, which was purified by column chromatography using hexaneas the eluting solvent to give the corresponding vinyl compounds.
62% With sodium hydroxide In solid thorough grounding a mixt. of aldehyde and phosphonium salt with NaOH atroom temp. under atmosphere for 1 min; extn. with CH2Cl2, drying with Na2SO4, filtration, evapn., chromy (SiO2,petroleum ether);
27% Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: ferrocenecarboxaldehyde In tetrahydrofuran at 0 - 20℃; for 10h; Inert atmosphere; General procedure A General procedure: In a 100 mL round-bottom flask equipped with a stir bar, methyltriphenylphosphonium bromide (1.2 equiv.) was dissolved in 50 ml THF under N2 atmosphere. Then, n-BuLi (1.2 equiv) was added dropwise at 0 (ice bath) and the mixture was stirred for 15 minutes. The aldehyde was dissolved in 10 ml of THF and the solution was then syringed through a septum. The mixture was stirred for 1 hour and maintained at 0 . It was then allowed to warm to room temperature and maintained under stirring for 9 hours. It was then quenched with water and extracted with ethyl acetate (3 x 50 ml). The combined organic layers were washed with H2O, brine and dried over by Na2SO4. The solvent was removed under reduced pressure and the residue was purified by chromatography on silica gel to give the corresponding alkene.

Reference: [1]Wang, Xiaowu; Kehr, Gerald; Daniliuc, Constantin G.; Erker, Gerhard [Journal of the American Chemical Society, 2014, vol. 136, # 8, p. 3293 - 3303]
[2]Valderrama, M.I. Reyes; García, R.A. Vázquez; Klimova; Klimova; Ortiz-Frade; García, M. Martínez [Inorganica Chimica Acta, 2008, vol. 361, # 6, p. 1597 - 1605]
[3]Miller, Edward J.; Weigelt, Carolyn A.; Serth, Judith A.; Rusyid, Rusydi; Brenner, Jeffery; et al. [Journal of Organometallic Chemistry, 1992, vol. 440, # 1.2, p. 91 - 101]
[4]Yu, Songjie; Noble, Adam; Bedford, Robin B.; Aggarwal, Varinder K. [Journal of the American Chemical Society, 2019, vol. 141, # 51, p. 20325 - 20334]
[5]Aukland, Miles H.; Talbot, Fabien J. T.; Fernández-Salas, José A.; Ball, Matthew; Pulis, Alexander P.; Procter, David J. [Angewandte Chemie - International Edition, 2018, vol. 57, # 31, p. 9785 - 9789][Angew. Chem., 2018, vol. 130, # 31, p. 9933 - 9937,5]
[6]Tang, Meizhong; Han, Shuxiong; Huang, Shenglan; Huang, Shenlin; Xie, Lan-Gui [Organic Letters, 2020, vol. 22, # 24, p. 9729 - 9734]
[7]Ravivarma, Mahalingam; Kumar, Kaliamurthy Ashok; Rajakumar, Perumal; Pandurangan, Arumugam [Journal of Molecular Liquids, 2018, vol. 265, p. 717 - 726]
[8]Liu, Wan-Yi; Xu, Qi-Hai; Ma, Yong-Xiang; Liang, Yong-Min; Dong, Ning-Li; Guan, De-Peng [Journal of Organometallic Chemistry, 2001, vol. 625, # 1, p. 128 - 131]
[9]Bigi, Franca; Camedda, Nicola; Cera, Gianpiero; Maestri, Giovanni; Maggi, Raimondo; Serafino, Andrea [Synthesis, 2020, vol. 52, # 12, p. 1762 - 1772]
  • 5
  • (2-ferrocenylethyl)trimethylammonium iodide [ No CAS ]
  • [ 1271-51-8 ]
YieldReaction ConditionsOperation in experiment
97% With potassium amide In ammonia
81% With potassium <i>tert</i>-butylate In benzene in boiling benzene;;
With sodium amalgam In water
With sodium In ammonia
51-85 With sodium hydroxide In sodium hydroxide 100°C;;
With sodium hydroxide In sodium hydroxide
With base In not given
In sodium hydroxide
With potassium amide In ammonia
With potassium <i>tert</i>-butylate In benzene in boiling benzene;
With sodium amalgam In water
With sodium In ethanol
With cyanides
With KOC(CH3)3 In benzene in boiling benzene;
With Na-amalgam In water
With Na In ethanol
With cyanides
In sodium hydroxide aq. NaOH;
With KNH2 In ammonia NH3 (liquid);

Reference: [1][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285] Fitzgerald, W. P. [Dissertation abstracts, Diss. Purdue Univ., Lafayette, Ind., 1963, S. 1/165, 1964, vol. 24, p. 2687]
[2]Pauson, P. L.; Watts, W. E. [Journal of the Chemical Society][Journal of the Chemical Society, 1963, p. 2990 - 2996] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285]
[3]Hauser, C. R.; Lindsay, J. K.; Lednicer, D. [Journal of Organic Chemistry, 1958, vol. 23, p. 358 - 361] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285]
[4]Slocum, D. W.; Jones, W. E.; Ernst, C. R. [Journal of Organic Chemistry, 1972, vol. 37, p. 4278 - 4281] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285]
[5][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285] Fitzgerald, W. P. [Dissertation abstracts, Diss. Purdue Univ., Lafayette, Ind., 1963, S. 1/165, 1964, vol. 24, p. 2687]
[6]Hauser, C. R.; Lindsay, J. K.; Lednicer, D. [Journal of Organic Chemistry, 1958, vol. 23, p. 358 - 361] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285]
[7]Lednicer, D.; Hauser, C. R. [Journal of Organic Chemistry, 1959, vol. 24, p. 43 - 46] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285]
[8]Hauser, C. R.; Lindsay, J. K.; Lednicer, D. [Journal of Organic Chemistry, 1958, vol. 23, p. 358 - 361] Lednicer, D.; Hauser, C. R. [Journal of Organic Chemistry, 1959, vol. 24, p. 43 - 46] Osberby, J. M.; Pauson, P. L. [Chemistry and industry][Chemistry and Industry (London, United Kingdom), 1958, p. 196 - 197]
[9]Hauser et al. [Journal of Organic Chemistry, 1957, vol. 22, p. 717][Journal of Organic Chemistry, 1958, vol. 23, p. 358] Hauser, C. R.; Lindsay, J. K.; Lednicer, D. [Journal of Organic Chemistry, 1958, vol. 23, p. 358 - 361] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285]
[10]Pauson, P. L.; Watts, W. E. [Journal of the Chemical Society][Journal of the Chemical Society, 1963, p. 2990 - 2996]
[11]Hauser, C. R.; Lindsay, J. K.; Lednicer, D. [Journal of Organic Chemistry, 1958, vol. 23, p. 358 - 361]
[12]Hauser, C. R.; Lindsay, J. K.; Lednicer, D. [Journal of Organic Chemistry, 1958, vol. 23, p. 358 - 361] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285]
[13]Lednicer, D.; Hauser, C. R. [Journal of Organic Chemistry, 1959, vol. 24, p. 43 - 46]
[14][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.1.4.3, page 80 - 89]
[15][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.1.4.3, page 80 - 89]
[16][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.1.4.3, page 80 - 89]
[17][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.1.4.3, page 80 - 89]
[18][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.1.4.3, page 80 - 89]
[19][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.1.4.3, page 80 - 89] Fitzgerald, W. P. [Dissertation abstracts, Diss. Purdue Univ. 1963, 1964, vol. 24, p. 2687]
  • 6
  • [ 1271-51-8 ]
  • 1-ethylferrocene [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With styrene; palladium diacetate In benzene under Ar or N2; Pd(OAc)2, Si compd. and Fe complex (molar ratio 1:100:50) added at room temp. to dried and distd. benzene; stirred for 7 h; centrifuged; filtrate passed through silica gel column;
32% With C35H32BF10P; hydrogen at 20℃; for 72h;
Stage #1: vinyl ferrocene With tris(pentafluorophenyl)borate; C57H41B2F20NP(1-)*H(1+) In benzene-d6 for 0.5h; Stage #2: With hydrogen In benzene-d6 at 20℃; 4.3. Catalytic hydrogenation General procedure: General procedure: In a J-Young NMR tube substrate(0.10 mmol), catalyst precursor 15 (23.5 mg, 0.02 mmol) andB(C6F5)3 (2.6 mg, 0.005 mmol) were dissolved in C6D6 (0.7 mL).After 30 min the atmosphere was removed, dihydrogen (2 bar)applied and the reaction monitored by 1H NMR spectroscopy.Conversion was determined from the 1H NMR spectra. (see theSupporting Information for control experiments and spectroscopicdata of hydrogenation products 17a-l).
  • 7
  • [ 1271-51-8 ]
  • polyvinylferrocene(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichromate anion In acetic acid
With {N(C6H4OCH3-p)3}(1+) In acetonitrile byproducts: {N(C6H4OCH3-p)3}; Electrochem. Process; 25°C; enthalpy of reaction and equil. constant given;;
With {N(C6H4OCH3-p)3}(1+) In acetonitrile byproducts: {N(C6H4OCH3-p)3}; Electrochem. Process; 25°C; enthalpy of reaction and equil. constant given;;
In not given Electrochem. Process; electrochemical oxidation;

  • 8
  • [ 1271-51-8 ]
  • (+/-)-{fc-CH-CH3}(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid In sulfuric acid
With sulfuric acid In sulfuric acid
With H2SO4 In sulfuric acid
Reference: [1]Horspool, W. M.; Sutherland, R. G. [Chemical Communications (London)][Chemical Communications (London), 1967, p. 786 - 788] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4.4, page 286 - 290]
[2]Cais, M.; Dannenberg, J. J.; Eisenstadt, A.; Levenberg, M. I.; Richards, J. H. [Tetrahedron Letters][Tetrahedron Letters, 1966, p. 1695 - 1701] Hisatome, M.; Yamakawa, K. [Tetrahedron, 1971, vol. 27, p. 2101 - 2110] Horspool, W. M.; Sutherland, R. G. [Chemical Communications (London)][Chemical Communications (London), 1967, p. 786 - 788] Turbitt, T. D.; Watts, W. E. [1974, p. 177 - 184] Turbitt, T. D.; Watts, W. E. [1974, p. 189 - 195] Turbitt, T. D.; Watts, W. E. [1974, p. 195 - 200] Williams, G. H.; Traficante, D.; Seyferth, D. [Journal of Organometallic Chemistry][Journal of Organometallic Chemistry, 1973, vol. 60, p. C 53 - C 56]
[3]Allenmark, S. [Tetrahedron Letters][Tetrahedron Letters, 1974, p. 371 - 374] Hill, E. A.; Wiesner, R. [Journal of the American Chemical Society, 1969, vol. 91, p. 509 - 510] Nesmeyanov, A. N.; Kazakova, L. I.; Reshetova, M. D.; Kazitsina, L. A.; Perevalova, E. G. [Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1970, p. 2639 - 2641][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1970, p. 2804 - 2806] Tirouflet, J.; Laviron, E.; Moise, C.; Mugnier, Y. [Journal of Organometallic Chemistry, 1973, vol. 50, p. 241 - 246] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.9.1.1, page 349 - 355] Cerichelli, G.; Floris, B.; Illuminati, G.; Ortaggi, G. [5th Intern. Conf. Organometal. Chem., Moscow 1971, Abstr., Bd. 1, S. 415/6]
  • 13
  • [ 1277-49-2 ]
  • [ 1271-51-8 ]
YieldReaction ConditionsOperation in experiment
97% With copper(II) sulfate In toluene byproducts: H2O; in boiling toluene;;
90% With potassium hydrogensulfate In benzene byproducts: H2O; in boiling benzene;;
84% In neat (no solvent) byproducts: H2O; 210°C, 20 Torr;;
84% With CuSO4; hydroquinone In toluene N2-atmosphere; refluxing Fe-complex with excess CuSO4 and traces of hydroquinone for 45 min; filtration, solvent removal (vac.), extn. into ether, drying (MgSO4), filtration, concn. (vac.), chromy. (SiO2, hexane), solvent removal (vac.);
76% With aluminum oxide; hydrogen cation In benzene byproducts: H2O; acidic Al2O3, ambient temp.;;
76% With Al2O3; H(1+) In benzene byproducts: H2O; acidic Al2O3, ambient temp.;;
72% Stage #1: 1-ferrocenylethanol With n-butyllithium In tetrahydrofuran at -50℃; for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: With C20H34ClO3P In tetrahydrofuran at -50 - 20℃; for 18h; Inert atmosphere; Schlenk technique;
55% In neat (no solvent) byproducts: H2O; 380-400°C;;
53% With aluminum oxide In benzene byproducts: H2O; neutral Al2O3, in boiling benzene;;
50% With aluminum oxide; hydrogen cation In benzene byproducts: H2O; acidic Al2O3, ambient temp.;;
50% With aluminum oxide In benzene byproducts: H2O; neutral Al2O3, in boiling benzene;;
50% With Al2O3; H(1+) In benzene byproducts: H2O; acidic Al2O3, ambient temp.;;
50% With activated neutral alumina In neat (no solvent) at 90 - 100℃;
42% With aluminum oxide In benzene byproducts: H2O; neutral Al2O3, in boiling benzene;;
22% With aluminum oxide; hydrogen cation In benzene byproducts: H2O; acidic Al2O3, ambient temp.;;
With acetic anhydride In pyridine byproducts: H2O; ambient temp.;;
With aluminum oxide In benzene byproducts: H2O; neutral Al2O3, in boiling benzene;;
With aluminum oxide In benzene neutral Al2O3, in boiling benzene;;
With cyclo-C6H11NCO In not given byproducts: H2O; 114-116°C;;
10-21 In neat (no solvent) byproducts: H2O, (C5H5FeC5H4CH(CH3))2O; 200°C, 36 Torr; high amt. of (C5H5FeC5H4CH(CH3))2O;;
81-89 In neat (no solvent) byproducts: H2O; 135-160°C, 11-35 Torr;;
10-21 In neat (no solvent) byproducts: H2O; 200°C, 36 Torr;;
With Al2O3 In benzene neutral Al2O3, in boiling benzene;;
With copper(II) sulfate; hydroquinone In toluene
1.59 g With dmap; methanesulfonyl chloride; triethylamine In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere; Vinylferrocene (4) Under an inert atmosphere, to a solution of alcohol 3 (2.00 g, 8.69mmol) and DMAP (53.1 mg, 0.43 mmol) in anhydrous CH 2 Cl 2 (20 mL)was added dropwise Et 3 N (3.64 mL, 26.1 mmol) at 0 °C, followed byaddition of methanesulfonyl chloride (0.45 mL, 9.14 mmol). The reac-tion mixture was then stirred at r.t. for 4 h. The reaction wasquenched by addition of 5% solution of NaHCO 3 (40 mL), and the mix-ture was extracted with CHCl 3 (3 × 100 mL). Collected organic layerswere washed with brine (100 mL), dried over Na 2 SO 4 , filtrated, andsolvent was removed under reduced pressure to afford the crudeproduct. The crude product was purified by chromatography on Al 2 O 3(hexanes/EtOAc, 9:1; R f = 0.8) to afford target product 4.Yield: 1.59 g (86%); yellow-orange solid; mp 50-52 °C (lit. 15 51-52 °C).IR (ATR): 1623, 1408, 1103, 1045, 998, 894, 810, 726, 517, 477, 446cm -1 .1 H NMR (600 MHz, CDCl 3 ): δ = 6.46 (dd, J = 17.4, 10.7 Hz, 1 H), 5.34 (d,J = 17.5 Hz, 1 H), 5.03 (d, J = 10.7 Hz, 1 H), 4.36 (s, 2 H), 4.21 (s, 2 H),4.11 (s, 5 H).13 C NMR (151 MHz, CDCl 3 ): δ = 134.7, 111.1, 83.7, 69.3, 68.7, 66.8.HRMS (ESI): m/z calcd for [M + H + ] C 12 H 13 Fe + : 213.0367; found:213.0359.Obtained spectral data are in agreement with those of the commer-cially available product.
With acetic anhydride In pyridine byproducts: H2O; ambient temp.;;
With copper(II) sulfate In toluene Reflux;

Reference: [1][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285] Current Patent Assignee: DUPONT DE NEMOURS INC - US3132165, 1964, A [C. A., 1964, vol. 61, p. 4396]
[2]Mechtler; Schloegl [Monatshefte fur Chemie, 1966, vol. 97, p. 754] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285]
[3][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285] Fitzgerald, W. P. [Dissertation abstracts, Diss. Purdue Univ., Lafayette, Ind., 1963, S. 1/165, 1964, vol. 24, p. 2687]
[4]Wang, Yu-Pin; Lui, Xen-Hum; Lin, Bi-Son; Tang, Wei-Der; Lin, Tso-Shen; Liaw, Jen-Hai; Wang, Yu; Liu, Yi-Hung [Journal of Organometallic Chemistry, 1999, vol. 575, # 2, p. 310 - 319]
[5][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285]
[6]Dixneuf, P.; Dabard, R. [Bulletin de la Societe Chimique de France][Bulletin de la Societe Chimique de France, 1972, p. 2838 - 2847]
[7]Korb, Marcus; Mahrholdt, Julia; Lang, Heinrich [European Journal of Inorganic Chemistry, 2017, vol. 2017, # 34, p. 4028 - 4048]
[8][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285] Fitzgerald, W. P. [Dissertation abstracts, Diss. Purdue Univ., Lafayette, Ind., 1963, S. 1/165, 1964, vol. 24, p. 2687]
[9]Massarskaya, S. M.; Sokolova, E. B.; Cherepakhina, G. V.; Korableva, A. V. [1969, vol. 61, p. 170 - 174][C. A., 1970, vol. 73, p. 99038] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285]
[10][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285]
[11]Sokolova, E. B.; Massarskaya, S. M.; Dyatlova, V. G.; Prokopova, L. K. [Zhurnal Obshchei Khimii, 1973, vol. 43, p. 2706 - 2709] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285]
[12]Schloegl; Mohar [Naturwissenschaften, 1961, vol. 48, p. 376] Schloegl, K.; Mohar, A. [Monatshefte fur Chemie][Monatshefte fuer Chemie, 1961, vol. 92, p. 219 - 235]
[13]Kaur, Sarbjeet; Van Steerteghem, Nick; Kaur, Paramjit; Clays, Koen; Singh, Kamaljit [Journal of Materials Chemistry C, 2016, vol. 4, # 41, p. 9717 - 9726]
[14]Goldberg, S. I.; Loeble, W. D.; Tidwell, T. T. [Journal of Organic Chemistry, 1967, vol. 32, p. 4070 - 4071] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285]
[15]Goldberg, S. I.; Loeble, W. D.; Tidwell, T. T. [Journal of Organic Chemistry, 1967, vol. 32, p. 4070 - 4071] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285]
[16][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285]
[17]Ayers, O. E.; Smith, T. G.; Burnett, J. D.; Ponder, B. W. [Analytical Chemistry, 1966, vol. 38, p. 1606 - 1607] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285]
[18]Nesmeyanov, A. N.; Kritskaya, I. I. [Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1964, p. 2061 - 2064][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1964, p. 2160 - 2165]
[19]Kieselack, P.; Lorkowski, H.-J. [Journal fur praktische Chemie (Leipzig 1954), 1970, vol. 312, p. 989 - 997] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285]
[20]U, G.-L.; Sokolova, E. B.; Leites, L. A.; Petrov, A. D. [Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1962, p. 826 - 830][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1962, p. 887 - 892] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285]
[21]Rausch, M. D.; Siegel, A. [Journal of Organometallic Chemistry, 1968, vol. 11, p. 317 - 324] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285]
[22][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2.4, page 283 - 285] Arimoto, F. S.; Haven, A. C. [Journal of the American Chemical Society, 1955, vol. 77, p. 6295 - 6297]
[23][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.2, page 279 - 281]
[24]Udomsap, Dutduan; Branger, Catherine; Culioli, Gérald; Dollet, Pascal; Brisset, Hugues [Chemical Communications, 2014, vol. 50, # 56, p. 7488 - 7491]
[25]Plevová, Kristína; Mudráková, Brigita; Šebesta, Radovan [Synthesis, 2018, vol. 50, # 4, p. 760 - 763]
[26]Current Patent Assignee: DUPONT DE NEMOURS INC - US2821512, 1958, A [C. A., 1958, p. 6842]
[27]Deriabin, Konstantin V.; Lobanovskaia, Ekaterina K.; Kirichenko, Sergey O.; Barshutina, Marie N.; Musienko, Pavel E.; Islamova, Regina M. [Applied Organometallic Chemistry, 2020, vol. 34, # 1]
  • 14
  • [ 1271-51-8 ]
  • [ 1122-91-4 ]
  • trans-(E)-4-[2-(ferrocenyl)ethenyl]benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With tetrabutylammonium tetrafluoroborate; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 80℃; Inert atmosphere; General procedure for the Palladium-Catalyzed coupling ofvinylferrocene A mixture of vinylferrocene (1 mmol), K2CO3 (2.5or 5 mmol), tetrabutylammonium tetrafluoroborat (2.5 or 5 mmol),the given amount of appropriate bromine-substituted compoundand catalytic amount of Pd(OAC)2 in 10 ml DMF was stirred at 80 °Cunder argon atmosphere overnight. After the completion of thereaction, the cooled mixture was filtered, diluted with CH2Cl2(50 ml) and washed with H2O (3 x 50 ml). The organic phase was dried over Na2SO4, filtered and the solvent was removed under thereduce pressure. The crude products were purified by columnchromatography on silica gel with hexane/EtOAC as eluent. Specificdetails for each compound are given below. 4-(2-Ferrocenylvinyl)benzaldehyde (3): from 0.1 g (0.47mmol)vinyl ferrocene and 0.08 g (0.47 mmol) 4-bromobenzaldehyde,0.11 g (0.36 mmol) red shining crystals was obtained in 88% yield:Rf 0.50 (Hexane: EtOAc 9:1); m.p. 150 °C, lit. [13] 150-151 °C; 1HNMR (400 MHz, CDCl3, 25 C): δ 9.97 (s, 1H, CHO), 7.83 (d, 2H,ArH), 7.56 (d. 2H, ArH), 7.07 (d, 3J (H,H) 16 Hz, 1H, CH), 6.72 (d, 3J(H,H) 16 Hz, 1H, CH), 4.50 (t, J 1.78 Hz, 2H, Cp), 4.35 (t,J 1.78 Hz, 2H, Cp), 4.15 (s, 5H, Cp) ppm; FT-IR (KBr, cm1): 3074,3062 (w), 2936, 2852 (w), 1685 (s), 1591, 1561 (w), 814 (w).
88% With tetrabutyl ammonium fluoride; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 80℃; Inert atmosphere;
80% With palladium diacetate; triethylamine In toluene (Ar); react. iron complex with aryl bromide in toluene at 115°C in the presence of Pd(OAc)2 and NEt3 (as in: R. Frantz et al. New J. Chem. 25 (2001) 188; R. Frantz et al. Eur. J. Inorg. Chem. (2002) 1088); silica gel column chromy. (toluene);
67.4% With triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide under N2; mixt. of vinylferrocene (8.51 mmol), aldehyde (3.87 mmol), Pd(OAc)2 (0.193 mmol) and phosphine (0.967 mmol) in Et3N/DMF (1/1) stirred at 120°C for 48 h; cooled, filtered, filtrate evapd., chromy. (SiO2, CH2Cl2/hexane (2/3)); elem. anal.;

  • 15
  • [ 1271-51-8 ]
  • [ 15164-44-0 ]
  • trans-(E)-4-[2-(ferrocenyl)ethenyl]benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In acetonitrile at 82℃; for 24h; Inert atmosphere; 4.2. Synthesis and characterization of aldehyde 1 Vinylferrocene (1.50 g, 7.07 mmol), 4-iodobenzaldehyde(0.684 g, 2.95 mmol), palladium(II) acetate (0.0331 g,0.147 mmol) and tri-o-tolyl-phosphine (0.224 g, 0.767 mmol) weredissolved in a 1:10 solution (v/v) of triethylamine and acetonitrile (30 ml). The dark red reaction mixturewas stirred under N2 at 82 Cfor 24 h. After cooling, the solvent was removed and resulting redresidue was dissolved in 25 ml DCM and 25 ml water added. Theorganic layer was separated and the aqueous layer washed withDCM (3 25 ml). The organic fractions were combined, stirred overanhydrous MgSO4 and removed by gravity filtration. The filtratewas collected and the solvent removed to give a dark red residue.The product was purified by column chromatography, initially usinga solvent system of 100% petroleum ether, followed by 50:50mixture of petroleum ether (40-60 C) and DCM. The desiredproduct (1) was isolated as a dark red powder (0.680 g, 73%). Mp:decomposition without melting, onset at 110 C. 1H NMR(399.951 MHz, CDCl3): d (ppm) 9.97 (s, 1H, CHO), 7.83 (d, 2H,J 8.3 Hz, ArH), 7.56 (d, 2H, J 8.4 Hz, ArH), 7.07 (d, 1H, J 16.1 Hz,HC]CH), 6.73 (d, 1H, J 16.1 Hz, HC]CH), 4.51 (t, 2H, Cp), 4.35 (t,2H, Cp), 4.16 (s, 5H, Cp). 13C{1H} NMR (100.635 MHz, CDCl3):d (ppm) 191.55, 144.07, 134.67, 131.52, 130.32, 126.07, 124.60,82.25, 69.76, 69.38, 67.37. IR (KBr, cm1) n 1693 (C]O), 1630 (C]C). EI-MS: m/z 316 ([M], 100%). Elemental Analysis forC19H16FeO0.5H2O calculated C, 70.18; H, 5.27, found C, 70.39; H,5.07%.
56% With palladium acetate; tributylamine; tri(ortho-tolyl)phosphane In N,N-dimethyl acetamide Ar, a soln. of Fe, I, Pd and N compds. stirred at room temp. for 1 h, P compd. added, stirred at room temp. for 3 h, heated at 100°C for 12 h; extd. (diethyl ether), org. phase washed (aq. HCl, water, brine), dried (MgSO4), solvent evapd., chromy. (silica gel, CH2Cl2/petroleum ether);
With palladium diacetate; triethylamine; Tri(p-tolyl)phosphine In acetonitrile at 90℃; for 24h; Inert atmosphere;
  • 17
  • [ 1271-51-8 ]
  • [ 626-39-1 ]
  • (E,E,E)-1,3,5-tris(2-ferrocenylvinyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With CH3COONa; tetrabutylammonium bromide In N,N-dimethyl-formamide (N2); heating a mixt. of iron complex, 1,3,5-tribromobenzene, sodium acetate, tetrabutylammonium bromide and palladium complex in DMF at 130°C for 16 h; evapn., sepn. with CH2Cl2/H2O/NaHCO3 mixt., drying with MgSO4, column chromy. (SiO2, CH2Cl2/acetone 10:1);
46% With K2CO3; NBu4Br In N,N-dimethyl-formamide under N2, in presence of Pd(OAc)2, heated in a capped pyrex tube for 2 d at 60°C; filtered, diluted with CH2Cl2, washed with water, organic phase dried (K2CO3), filtered, solvent removed in vac., column chromy. (silica gel, petroleum ether/CH2Cl2 1:1); elem. anal.;
  • 18
  • [ 1271-51-8 ]
  • 4R,5R-4-methyl-3-isopropyl-5-phenyl-1,3,2-oxaazaborolidine [ No CAS ]
  • (E)-(4R,5R-4-methyl-3-isopropyl-5-phenyl-1,3,2-oxaazaborolidyl)(ferrocenyl)ethene [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% In toluene byproducts: ferrocenylethane; under Ar; to a soln. of the Rh-complex in toluene was added the arylethene, reaction with the oxaazaborolidine for 4 h; distn.;
  • 19
  • [ 1271-51-8 ]
  • [ 38186-51-5 ]
  • C5H5FeC5H4C2H2C6H4CH2PO(OC2H5)2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With tris(o-tolyl)phosphine; triethylamine In toluene mixed, heated at 115°C with stirring for 48 h; cooled to room temp., filtered, evapd., chromy.(silica-diethyl ether), evapd., elem. anal.;
  • 20
  • [ 1271-51-8 ]
  • (E,E)-1,1'-bis[p-bromophenyl-ethenyl]ferrocene [ No CAS ]
  • (C5H4)2Fe(CHCHC6H4CHCHC5H4FeC5H5)2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With AcONa; n-Bu4NBr In not given a mixt. of vinylferrocene (1.5 mmol), FeBr-contg. compd. (0.73 mmol), anhyd. AcONa (2.4 mol), n-Bu4NBr (0.2 mmol) and Pd catalyst (0.02 mmol) inDMA was heated at 130°C for 5 h; the solvent was removed; the complex was extd. with a CH2Cl2/H2O mixt. and the org. phase was dried over MgSO4; column chromy. on silica gel; washing with hexane; hexane/CH2Cl2 (1:3) as eluent; recrystn. from CH2Cl2/hexane; elem. anal.; (1)H NMR spectra;
  • 21
  • [ 1271-51-8 ]
  • [ 56990-02-4 ]
  • (C5H5FeC5H4CHCH)2C6H3CHO [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: A stirred mixture of bromo compound (1.0 equiv.), Pd(OAc)2 (0.1/0.2 equiv.) in dry DMF (25mL) under nitrogen was successively treatedwith K2CO3 (3.0/6.0 equiv.) and tetrabutylammoniumbromide (0.1/0.2equiv.)and stirred for 30 min. The vinyl dendron (1.0/2.0 equiv.)wasthen added and the resulting mixture was stirred at 90 C for 12 h,cooled and filtered. The filtrate was evaporated to dryness in vacuo.The residue was extracted with CHCl3 (3 × 100 mL), washed withwater (3 × 100 mL) and dried over anhydrous Na2SO4. Evaporation ofthe organic layer afforded the crude product,whichwas purified by columnchromatography using the eluent as mentioned under each compoundto afford the corresponding conjugated dendrimers.
  • 22
  • [ 1271-51-8 ]
  • [ 7511-49-1 ]
  • (C5H5FeC5H4CHCHC6H4)3C6H3 [ No CAS ]
  • 23
  • [ 1271-51-8 ]
  • [ 29102-67-8 ]
  • ((C5H5FeC5H4CHCH)2C6H3)3C6H3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With NaOOCCH3; Bu4NBr In N,N-dimethyl acetamide heating at 130 °C for 15-20 h; solvent was removed in vac., residue was extd. with CH2Cl2-H2O-NaHCO3, org. phase was dried with MgSO4, chromy. (silica, hexane:CH2Cl2=7:3), elem. anal.;
  • 24
  • [ 1271-51-8 ]
  • [ 20677-12-7 ]
  • C5H5FeC5H4C2H2C6H4PO(OC2H5)2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With tris(o-tolyl)phosphine; triethylamine In toluene mixed, heated at 115°C with stirring for 48 h; cooled to room temp., filtered, evapd., chromy.(silica-diethyl ether), evapd., elem. anal.;
  • 25
  • [ 172222-30-9 ]
  • [ 1271-51-8 ]
  • [ 75-09-2 ]
  • [(tricyclohexylphosphine)2Cl2RuCH(ferrocenyl)]*CH2Cl2 [ No CAS ]
  • 26
  • [ 1271-51-8 ]
  • [ 3814-34-4 ]
  • (E)-(4-ethyl-1-hexenyl)ferrocene [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With bis(cyclopentadienyl)titanium dichloride; butyl magnesium bromide In diethyl ether Ti compd. was added to mixt. of Fe complex, 1-bromo-2-ethylbutane and n-BuMgCl in Et2O at 0°C under N2; mixt. was stirred for 5 h; aq. HCl added at 0°C; warmed to room temp.; satd. aq. soln. of NH4Cl added; extd. (ether); dried (MgSO4); evapd.; chromd. (CHCl3); elem. anal.;
  • 27
  • [ 1271-51-8 ]
  • [ 23488-38-2 ]
  • 2,3,5,6-tetrakis(2-ferrocenylvinyl)-p-xylene [ No CAS ]
  • 28
  • [ 1085568-96-2 ]
  • [ 2169-87-1 ]
  • [ 1271-51-8 ]
  • [ 300702-85-6 ]
  • 29
  • [ 167859-41-8 ]
  • [ 1271-51-8 ]
  • N-[4-(2-ferrocenylvinyl)phenyl]-N,N-bis(4-formylphenyl)amine [ No CAS ]
  • 30
  • [ 1271-51-8 ]
  • [ 4181-20-8 ]
  • C54H45Fe3N [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tributyl-amine;tri-tert-butyl phosphine; palladium diacetate; In 1,4-dioxane; for 96h;Inert atmosphere; Reflux; About 424 mg (about 2 mmol) of vinylferrocene, about 312 mg (about 0.5 mmol) of <strong>[4181-20-8]tris(4-iodophenyl)amine</strong> and about 7 mg (about 6 mol percent) of palladium acetate were placed in a flask. After a reflux condenser was connected to the flask, about 3 ml of 1,4-dioxene as a solvent, about 480 mul (about 2 mmol) of tri-n-butylamine as a base and about 11 mul (about 9 mol percent) of tri-t-butylphosphine were injected into the flask using a syringe under a nitrogen atmosphere. The solution was degassed with nitrogen gas, and refluxed in an oil bath. The reaction was allowed to proceed for about 4 days. The reaction solution was diluted with about 10 ml of methylene chloride and neutralized with a saturated aqueous solution of ammonium chloride. The neutralized solution was transferred to a separatory funnel, followed by phase separation. The obtained organic layer was dried over anhydrous magnesium sulfate and passed through a glass filter to obtain a transparent polymer solution. The polymer solution was evaporated under reduced pressure to remove the solvents. The residue was purified by column chromatography using toluene/hexane (1/2), yielding the metallocenyl dendrimer (about 301 mg) of Formula 2 as an orange solid. The 1H-NMR spectrum of the metallocenyl dendrimer is shown in FIG. 3.
  • 31
  • [ 1271-51-8 ]
  • [ 73183-34-3 ]
  • [(1E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]-ferrocene [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With AlEt3 In toluene 1 equiv. B2pin2, 60°C, 6 h;
93% With (CH3Si(C6H4P(C6H3(CF3)2)2)2)Pd(SO3CF3); triethylaluminum In toluene at 60℃; for 6h; Inert atmosphere; regioselective reaction;
  • 32
  • [ 1271-51-8 ]
  • [ 73183-34-3 ]
  • [ 1325764-16-6 ]
YieldReaction ConditionsOperation in experiment
92% With AlEt3 In toluene 2 equiv. B2pin2, 60°C, 6 h;
92% With (CH3Si(C6H3(CF3)P(C6H3(CF3)2)2)2)Pd(SO3CF3); triethylaluminum In toluene at 60℃; for 6h; Inert atmosphere; regioselective reaction;
  • 33
  • [ 1271-51-8 ]
  • [ 1401072-73-8 ]
  • [ 1401082-84-5 ]
YieldReaction ConditionsOperation in experiment
93% at 80℃; for 3h; Inert atmosphere; Microwave irradiation; 2 2-(9H-fluoren-9-ylidene)-3-(penta(ferrocenyl)cyclopentadienyl)-5- oxopyrazolidin-2-ium-l-ide (Table 3, 5mm). General procedure: Synthesized according to general procedure C using hydrazone (0.0800 g, 0.255 mmol), vinyl-ferrocene (0.0541 g, 0.255 mmol) in trifiuorotoluene (1.28 mL) and heated at 80 °C for three hours. Volatiles were removed and the crude product was isolated by column chromatography with 100% CH2CI2, then 50% EtOAc/w-hexanes and gradually increased to 100% EtOAc. The title compound was obtained as dark red crystals (0.1024 g, 0.237 mmol, 93 % isolated yield). TLC Rf = 0.22 in 100 % EtOAc. ¾ NMR (CDC13, 300 MHz) δ ppm 8.90 (d, J = 7.6, 1H), 7.97 (dd, J = 7.1, 4.0, 2H), 7.62-7.48 (m, 4H), 7.30 (t, J = 7.5, 1H), 6.35-6.33 (m, 1H), 4.36 (d, J = 20.6, 2H), 4.15 (d, J = 0.3, 1H), 3.84 (s, 1H), 3.34-3.33 (m, 12H), 3.14 (d, J = 15.7, 1H); 13C NMR (CDC13, 100 MHz) δ ppm 184.3, 140.7, 139.9, 138.3, 132.2 (CH), 131.1 (CH), 130.3 (CH), 129.8 (C), 129.3 (CH), 128.6 (CH), 127.0 (CH), 121.5 (CH), 120.9 (CH), 89.2 (C), 69.5 (CH), 69.3 (CH), 67.8 (CH), 67.5 (CH), 67.4 (CH), 66.6 (CH), 40.4 (CH2); IR (film); 3086, 2975, 1664, 1546, 1273, 1120, 733 cm"1; HRMS (EI): Exact mass calcd for C28H26FeiN20i[M]+: 432.0925; found: 432.0951.
93% at 80℃; for 3h; Inert atmosphere;
93% at 80℃; for 3h; Microwave irradiation; Sealed tube;
  • 34
  • [ 870004-04-9 ]
  • [ 1271-51-8 ]
  • 1,2-diferrocenylethylene [ No CAS ]
  • C24H27BFeO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 43℃; for 6h; Inert atmosphere; General procedure for the CM reaction of 4: General procedure: (E)-4,4,5,5-Tetramethyl-2-(4-styrylphenyl)-1,3,2-dioxaborolane 7a. Boronate 4a (113 mg, 0.49 mmol), styrene 5a (281 µL, 0.91 gmL-1, 2.45 mmol), Grubbs’ catalyst 6b (12 mg, 0.015 mmol), and CH2Cl2 (5 mL) were mixed in a round-bottomed flask and stirred under reflux (~ 45 °C) and nitrogen atmosphere for 6 hours. The mixture was cooled to rt, the volatiles were removed under reduced pressure and the crude product purified by flash chromatography on silica gel, hexane/CH2Cl2 6:4, to give 97 mg of the pure expected product as a white solid in 65% yield, (E)-isomer only.
  • 35
  • [ 1271-51-8 ]
  • [ 196316-31-1 ]
  • pseudo-para-bis(ferrocenylvinyl)[2.2]paracyclophane [ No CAS ]
  • C40H36Fe2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 31% 2: 39% With tetrabutylammomium bromide; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 95℃; for 20h; Schlenk technique; Synthesis of pseudo-para bis(2-ferrocenylvinyl)-[2.2]-paracyclophane, 2 A deoxygenated mixture of vinylferrocene (636 mg, 3.0 mmol), K2CO3 (5.52 g, 40 mmol), tetrabutylammonium bromide (4.51 g, 14 mmol), pseudo-para dibromo-[2.2]-paracyclophane [61] (366.1 mg, 1.0 mmol) and Pd(OAc)2 (67 mg, 0.3 mmol) in DMF (43 mL) was heated at 95 °C for 20 h. After cooling to r.t. the dark reaction mixture was filtered, diluted with CH2Cl2 (~40 mL) and washed with brine (4 x 30 mL). The organic phase was dried with MgSO4, filtered and the solvent was removed from the filtrate in vacuo. The residuewas subjected to chromatography on deactivated Al2O3 (n-hexane). Two fractions containing productswere collected: a first one containing 3 (270 mg, 31%) and a second one containing 2. Slightly impure 2was again subjected to columnchromatography on silica gel with CHCl3 followed by crystallization from a CHCl3/MeOH mixture. 2 was obtained as an orange solid in a yield of 245 mg, 39%.
  • 36
  • [ 1271-51-8 ]
  • [ 51483-92-2 ]
  • (E)-6-ferrocenylvinyl-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With tetrabutylammomium bromide; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 95℃; for 19h; Schlenk technique; 4.2 General procedure for the synthesis of bioconjugates 4-6 General procedure: A deoxygenated mixture of vinylferrocene (170mg, 0.80mmol), K2CO3 (1.50g, 11mmol), tetrabutylammonium bromide (1.19g, 3.70mmol), bromochromone (0.66mmol) and Pd(OAc)2 (20mg, 0.09mmol) in DMF (23ml) was heated at 95°C for 19h. After cooling to r. t. the reaction mixture was evaporated to dryness. Solid residue was dissolved in chloroform and extracted several times with water. The organic phase was dried with MgSO4, filtered and the solvent was removed from the filtrate in vacuo. The residue was subjected to chromatography on SiO2 (eluent: CHCl3/methanol, 50:2). Finally the analytically pure products were obtained after recrystallization from chloroform/n-hexane mixture.
  • 37
  • [ 1271-51-8 ]
  • [ 30779-63-6 ]
  • (E)-6-ferrocenylvinyl-2-methyl-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With tetrabutylammomium bromide; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 95℃; for 19h; Schlenk technique; 4.2 General procedure for the synthesis of bioconjugates 4-6 General procedure: A deoxygenated mixture of vinylferrocene (170mg, 0.80mmol), K2CO3 (1.50g, 11mmol), tetrabutylammonium bromide (1.19g, 3.70mmol), bromochromone (0.66mmol) and Pd(OAc)2 (20mg, 0.09mmol) in DMF (23ml) was heated at 95°C for 19h. After cooling to r. t. the reaction mixture was evaporated to dryness. Solid residue was dissolved in chloroform and extracted several times with water. The organic phase was dried with MgSO4, filtered and the solvent was removed from the filtrate in vacuo. The residue was subjected to chromatography on SiO2 (eluent: CHCl3/methanol, 50:2). Finally the analytically pure products were obtained after recrystallization from chloroform/n-hexane mixture.
  • 38
  • [ 1271-51-8 ]
  • [ 1218-80-0 ]
  • (E)-6-ferrocenylvinyl-2-phenyl-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With tetrabutylammomium bromide; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 95℃; for 19h; Schlenk technique; 4.2 General procedure for the synthesis of bioconjugates 4-6 General procedure: A deoxygenated mixture of vinylferrocene (170mg, 0.80mmol), K2CO3 (1.50g, 11mmol), tetrabutylammonium bromide (1.19g, 3.70mmol), bromochromone (0.66mmol) and Pd(OAc)2 (20mg, 0.09mmol) in DMF (23ml) was heated at 95°C for 19h. After cooling to r. t. the reaction mixture was evaporated to dryness. Solid residue was dissolved in chloroform and extracted several times with water. The organic phase was dried with MgSO4, filtered and the solvent was removed from the filtrate in vacuo. The residue was subjected to chromatography on SiO2 (eluent: CHCl3/methanol, 50:2). Finally the analytically pure products were obtained after recrystallization from chloroform/n-hexane mixture.
  • 39
  • 3-(6-bromo-4-oxo-4H-chromen-3-yl)propanoic acid [ No CAS ]
  • [ 1271-51-8 ]
  • (E)-6-ferrocenylvinyl-chromen-4-one-3-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With tetrabutylammomium bromide; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 95℃; for 19h; Schlenk technique; 4.2.4 Synthesis of (E)-6-ferrocenylvinyl-chromen-4-one-3-propionic acid 7 A deoxygenated mixture of vinylferrocene (170mg, 0.80mmol), K2CO3 (1.50g, 11mmol), tetrabutylammonium bromide (1.19g, 3.70mmol), 6-bromochromone-3-propionic acid (196.8mg, 0.66mmol) and Pd(OAc)2 (20mg, 0.09mmol) in DMF (23ml) was heated at 95°C for 19h. After cooling to r. t. the reaction mixture was evaporated to dryness. Solid residue was dissolved in chloroform and extracted six times with water followed by extraction with 3.5% HClaq. The organic phase was dried with MgSO4, filtered and the solvent was removed from the filtrate in vacuo. The residue was subjected to chromatography on SiO2 (eluent: CHCl3/methanol, 50:5). Finally the analytically pure products were obtained after recrystallization from DMSO/water.
  • 40
  • [ 1271-51-8 ]
  • [ 624-31-7 ]
  • (E)-1-ferrocenyl-2-(4-methylphenyl)ethene [ No CAS ]
  • [ 1555883-56-1 ]
YieldReaction ConditionsOperation in experiment
1: 32% 2: 16% With C18H19Cl2N2PPd; triethylamine In N,N-dimethyl-formamide at 140℃; for 2h; Inert atmosphere; Schlenk technique; 4.2.3. General procedure for Mizoroki-Heck coupling reactions. General procedure: In a 25-mL round-bottomed flask, a mixture of aryl iodide (5 mmol), alkene (6 mmol), and base (5.6 mmol) was placed in 4 mL of DMF, then a solution of the complex 3 (0.005 mol %) in 1 mL of DMF was added. The reaction mixture was refluxed for the time stated in Tables 3 and 4 at 140 °C. The reaction mixture was poured into water (20 mL) and extracted with ether or hexane (2×30 mL). The combined organic layers were dried over anhydrous sodium sulfate. After the removal of the solvent in vacuo, the resulting crude was purified by column chromatography on silica gel (hexane/ethyl acetate) to give the corresponding cross-coupling product (the purified product was identified by means of determination of mp and by 1H and 13C NMR, the data obtained are consistent with literature).26 The entire flasks used in the each coupling reaction were meticulously cleaned with aqua regia to avoid the presence of unseen palladium catalyst.
  • 41
  • [ 1271-51-8 ]
  • ethylferrocenium [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With C30H33FeP; hydrogen; bis(pentafluorophenyl)borohydride In (2)H8-toluene at 80℃; for 16h;
  • 42
  • [ 1271-51-8 ]
  • [ 188047-98-5 ]
  • [ 1627688-30-5 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In chloroform at 60℃; 6.2.1. Thiaflavans prepared by the synthetic protocol A General procedure: As shown as the synthetic protocol A in Scheme 2, compounds 1-11 were synthesized following literature description [16] with m-methoxyphenol, p-methoxyphenol, resorcinol, and hydroquinone as reagents. One hydroxyl group in resorcinol and hydroquinone was protected by tert-butyldimethylsilyl chloride. Then, 17 mL of dry CHCl3 solution containing excess PhtNSCl was added dropwisely to 8 mL of dry CHCl3 solution containing monoprotected hydroquinone or resorcinol and stirred for 16 h at 0 °C until phenols cannot be detected by thin layer chromatography (TLC). The mixture was diluted with CH2Cl2 and washed by saturated NaHCO3 and water. The organic phase was dried over anhydrous Na2SO4, and the solvent was removed under vacuum. The residue was purified by column chromatography with CH2Cl2 as the eluent to afford thiophthalimides as colorless solid. The following cycloaddition reactions were carried out in dry CHCl3 solution of thiophthalimides (~ 0.1 M) and styrenes (2 equiv.) or vinyl ferrocene (2 equiv.) and freshly distilled (C2H5)3N (2 equiv.) at 60 °C. The reaction was finished with thiophthalimides not detected by TLC. Then, the solvent was evaporated under vacuum pressure, and the residual solid was purified with column chromatography to afford silylated adducts. The desilylation operation was performed in dry tetrahydrofuran (THF) solution containing 0.04 M aforementioned adducts at 0 °C, to which a solution of (n-C4H9)4NF*3H2O in THF (1 equiv. for each protective group) was added. The reaction was finished with the reagent not detected by TLC, and then the mixture was diluted with ethyl acetate and washed with saturated NH4Cl and water. The organic layer was dried over anhydrous Na2SO4, and the solvent was evaporated under vacuum pressure. The residue was purified with column chromatography to afford thiaflavans.
  • 43
  • [ 1271-51-8 ]
  • [ 178161-08-5 ]
  • [ 1616401-35-4 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In chloroform at 60℃; 6.2.1. Thiaflavans prepared by the synthetic protocol A General procedure: As shown as the synthetic protocol A in Scheme 2, compounds 1-11 were synthesized following literature description [16] with m-methoxyphenol, p-methoxyphenol, resorcinol, and hydroquinone as reagents. One hydroxyl group in resorcinol and hydroquinone was protected by tert-butyldimethylsilyl chloride. Then, 17 mL of dry CHCl3 solution containing excess PhtNSCl was added dropwisely to 8 mL of dry CHCl3 solution containing monoprotected hydroquinone or resorcinol and stirred for 16 h at 0 °C until phenols cannot be detected by thin layer chromatography (TLC). The mixture was diluted with CH2Cl2 and washed by saturated NaHCO3 and water. The organic phase was dried over anhydrous Na2SO4, and the solvent was removed under vacuum. The residue was purified by column chromatography with CH2Cl2 as the eluent to afford thiophthalimides as colorless solid. The following cycloaddition reactions were carried out in dry CHCl3 solution of thiophthalimides (~ 0.1 M) and styrenes (2 equiv.) or vinyl ferrocene (2 equiv.) and freshly distilled (C2H5)3N (2 equiv.) at 60 °C. The reaction was finished with thiophthalimides not detected by TLC. Then, the solvent was evaporated under vacuum pressure, and the residual solid was purified with column chromatography to afford silylated adducts. The desilylation operation was performed in dry tetrahydrofuran (THF) solution containing 0.04 M aforementioned adducts at 0 °C, to which a solution of (n-C4H9)4NF*3H2O in THF (1 equiv. for each protective group) was added. The reaction was finished with the reagent not detected by TLC, and then the mixture was diluted with ethyl acetate and washed with saturated NH4Cl and water. The organic layer was dried over anhydrous Na2SO4, and the solvent was evaporated under vacuum pressure. The residue was purified with column chromatography to afford thiaflavans.
  • 44
  • [ 865541-56-6 ]
  • [ 1271-51-8 ]
  • [ 1627688-29-2 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In chloroform at 60℃; 6.2.1. Thiaflavans prepared by the synthetic protocol A General procedure: As shown as the synthetic protocol A in Scheme 2, compounds 1-11 were synthesized following literature description [16] with m-methoxyphenol, p-methoxyphenol, resorcinol, and hydroquinone as reagents. One hydroxyl group in resorcinol and hydroquinone was protected by tert-butyldimethylsilyl chloride. Then, 17 mL of dry CHCl3 solution containing excess PhtNSCl was added dropwisely to 8 mL of dry CHCl3 solution containing monoprotected hydroquinone or resorcinol and stirred for 16 h at 0 °C until phenols cannot be detected by thin layer chromatography (TLC). The mixture was diluted with CH2Cl2 and washed by saturated NaHCO3 and water. The organic phase was dried over anhydrous Na2SO4, and the solvent was removed under vacuum. The residue was purified by column chromatography with CH2Cl2 as the eluent to afford thiophthalimides as colorless solid. The following cycloaddition reactions were carried out in dry CHCl3 solution of thiophthalimides (~ 0.1 M) and styrenes (2 equiv.) or vinyl ferrocene (2 equiv.) and freshly distilled (C2H5)3N (2 equiv.) at 60 °C. The reaction was finished with thiophthalimides not detected by TLC. Then, the solvent was evaporated under vacuum pressure, and the residual solid was purified with column chromatography to afford silylated adducts. The desilylation operation was performed in dry tetrahydrofuran (THF) solution containing 0.04 M aforementioned adducts at 0 °C, to which a solution of (n-C4H9)4NF*3H2O in THF (1 equiv. for each protective group) was added. The reaction was finished with the reagent not detected by TLC, and then the mixture was diluted with ethyl acetate and washed with saturated NH4Cl and water. The organic layer was dried over anhydrous Na2SO4, and the solvent was evaporated under vacuum pressure. The residue was purified with column chromatography to afford thiaflavans.
  • 45
  • [ 1271-51-8 ]
  • [ 160855-15-2 ]
  • [ 1616401-39-8 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In chloroform at 60℃; 6.2.1. Thiaflavans prepared by the synthetic protocol A General procedure: As shown as the synthetic protocol A in Scheme 2, compounds 1-11 were synthesized following literature description [16] with m-methoxyphenol, p-methoxyphenol, resorcinol, and hydroquinone as reagents. One hydroxyl group in resorcinol and hydroquinone was protected by tert-butyldimethylsilyl chloride. Then, 17 mL of dry CHCl3 solution containing excess PhtNSCl was added dropwisely to 8 mL of dry CHCl3 solution containing monoprotected hydroquinone or resorcinol and stirred for 16 h at 0 °C until phenols cannot be detected by thin layer chromatography (TLC). The mixture was diluted with CH2Cl2 and washed by saturated NaHCO3 and water. The organic phase was dried over anhydrous Na2SO4, and the solvent was removed under vacuum. The residue was purified by column chromatography with CH2Cl2 as the eluent to afford thiophthalimides as colorless solid. The following cycloaddition reactions were carried out in dry CHCl3 solution of thiophthalimides (~ 0.1 M) and styrenes (2 equiv.) or vinyl ferrocene (2 equiv.) and freshly distilled (C2H5)3N (2 equiv.) at 60 °C. The reaction was finished with thiophthalimides not detected by TLC. Then, the solvent was evaporated under vacuum pressure, and the residual solid was purified with column chromatography to afford silylated adducts. The desilylation operation was performed in dry tetrahydrofuran (THF) solution containing 0.04 M aforementioned adducts at 0 °C, to which a solution of (n-C4H9)4NF*3H2O in THF (1 equiv. for each protective group) was added. The reaction was finished with the reagent not detected by TLC, and then the mixture was diluted with ethyl acetate and washed with saturated NH4Cl and water. The organic layer was dried over anhydrous Na2SO4, and the solvent was evaporated under vacuum pressure. The residue was purified with column chromatography to afford thiaflavans.
  • 46
  • [ 12093-10-6 ]
  • [ 2065-66-9 ]
  • [ 1271-51-8 ]
YieldReaction ConditionsOperation in experiment
97% Stage #1: methyl-triphenylphosphonium iodide With dibenzo-18-crown-6; potassium <i>tert</i>-butylate In tetrahydrofuran at 22℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: ferrocenecarboxaldehyde In tetrahydrofuran at 22℃; for 16h; Inert atmosphere; Schlenk technique;
With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 21.5h;
  • 47
  • [ 1271-51-8 ]
  • (E)-4-Bromo-7-(2-(pyridin-4-yl)vinyl)benzo[c][1,2,5]thiadiazole [ No CAS ]
  • 4-((E)-2-ferocenylvinyl)-7-((E)-2-(pyridin-4-yl)vinyl)benzo[c][1,2,5]thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With tetrabutylammomium bromide; sodium acetate; palladium diacetate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; 6 4.2.1
(E)-4-(Piperidin-1-yl)-7-(2-(pyridin-4 yl)vinyl)benzo[c][1,2,5]thiadiazole (3a) General procedure: A mixture of 4-bromo-7-(piperidin-1-yl)benzo[c][1,2,5]thiadiazole (2a) (0.298 g, 1 mmol), 4-vinylpyridine (0.115 g, 1.1 mmol), Pd(OAc)2 (5.0 mg, 0.022 mmol), NaOAc (0.82 g, 10 mmol), n-Bu4NBr (0.065 g, 0.2 mmol) and N,N-dimethylformamide (10 mL) was heated at 100 °C for 24 h under nitrogen atmosphere. After cooling, the reaction was quenched by adding excess water. The precipitate formed was filtered, washed with water, dissolved in dichloromethane, and dried over anhydrous sodium sulfate. After evaporation of the volatiles, the residue was purified by column chromatography on silica gel, using a hexanes/dichloromethane mixture (2:3) as eluant to obtain the title compound 3a. 4.2.6 4-((E)-2-Ferocenylvinyl)-7-((E)-2-(pyridin-4-yl)vinyl)benzo[c][1,2,5]thiadiazole (6c) Compound 6c (0.277 g, 73%) was prepared as dark solid by following a procedure similar to that described above for 6a by using vinylferrocene. Rf (70% CH2Cl2/hexanes) 0.39; mp 184-186 °C; νmax (KBr film) 2924, 2847, 1622, 1380, 1100, 965, 810 cm-1; δH (500.13 MHz, CDCl3) 4.19 (5H, s, Cp), 4.40 (2H, s, Cp), 4.62 (2H, s, Cp), 7.22 (1H, s), 7.50 (2H, s), 7.61 (1H, buried d, vinyl), 7.69 (1H, d, J=6.0 Hz), 7.75 (1H, d, J=16.0 Hz, vinyl), 7.84 (1H, d, J=16.0 Hz, vinyl), 7.99 (1H, d, J=16.0 Hz, vinyl), 8.6 (2H, br s, pyridine); δC (125.77 MHz, CDCl3) 67.5, 69.5, 69.9, 83.0, 121.0, 121.5, 125.2, 126.8, 129.1, 129.2, 129.8, 131.2, 134.0, 145.0, 150.2, 153.7, 153.9; HRMS (ESI): MH+, found 449.0625. C25H19FeN3S requires 449.0649.
  • 48
  • [ 31904-34-4 ]
  • [ 1271-55-2 ]
  • [ 1271-51-8 ]
  • 49
  • [ 1271-51-8 ]
  • [ 135654-49-8 ]
  • ((1RS,2RS)-2-(trifluoromethyl)cyclopropyl)ferrocene [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With meso-tetraphenylporphyrin iron(III) chloride; cesium fluoride In N,N-dimethyl acetamide at 20℃; for 0.5h; Inert atmosphere; diastereoselective reaction;
  • 50
  • [ 12093-10-6 ]
  • [ 1271-66-5 ]
  • [ 1271-51-8 ]
YieldReaction ConditionsOperation in experiment
62% In tetrahydrofuran; toluene at 80℃; for 10h; Inert atmosphere; Schlenk technique; General procedure for reactions of Cp2TiMe2 with carbonyl compounds General procedure: A 100mL dry, nitrogen purged round bottom flask was charged with the carbonyl compound in dry tetrahydrofuran. Freshly prepared Cp2TiMe2 in toluene was added. The reaction mixture was heated to 80°C for 10h and was monitored by thin layer chromatography. Insoluble precipitate was separated, the solvent evaporated under reduced pressure, and the residue obtained was purified by column chromatography.
  • 51
  • [ 1271-51-8 ]
  • [ 94598-10-4 ]
YieldReaction ConditionsOperation in experiment
94% Stage #1: vinyl ferrocene With potassium hydroxide In ethanol at 0℃; for 0.5h; Stage #2: With N-iodo-succinimide In ethanol at 0 - 20℃; for 2.5h; 5.1.2. Iodoethynylferrocene (2) Ethynylferrocene (1) (0.5 g, 2.380 mmol) was dissolved in dryethanol (35 mL) and cooled to 0 °C and subsequently treated withsolid KOH (0.340 g, 6 mmol). After 30 min of stirring at a lowtemperature solid N-iodosuccinimide (0.642 g, 2.856 mmol) wasadded to the mixture, and the stirring continued at 0 °C for additional30 min. The cold bath was then removed and the stirringcontinued at room tempreture for an additional 2 h. Aftercompletion of reaction (monitored by TLC) 100 mL of EtOAc wasadded and the mixture extracted three times with brine. Theorganic layer was separated, dried over Na2SO4, filtered, andevaporated. The productwas isolated in quantitative yield as brownSolid.Yield: 94% (brown solid); m.p 112-115 °C (lit. 116-117 C) [47];1H NMR (500 MHz, CDCl3): δ 4.18-4.23 (m, 7H), 4.44-4.47 (m,2H) ppm; 13C NMR (75 MHz, CDCl3): δ 66.4, 69.4, 69.5, 70.6, 70.7,70.77, 70.84, 70.9, 72.5, 74.3, 92.8 ppm.
  • 52
  • [ 1271-51-8 ]
  • [ 819-19-2 ]
  • (R)-1-ferrocenylethylditert-butylphosphine [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With 2,6-bis(3,5-dimethylphenyl)-4-hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide In toluene at 60℃; for 10h; Inert atmosphere; 1.1 Example 1(1) (R) -1- ferrocenyl ethyl di-t-butyl phosphine synthesis Under argon, into a dried reactor were added successively vinyl ferrocene (1mol, 212g), (R ) -3,3'-bis (3,5-dimethylphenyl) -1,1 ' - binaphthol phosphonate (0.01mol, 5.6g) and 1L of toluene, followed by addition of di-tert-butylphosphine (1mol, 147g), heated to 60 deg.] C for 12 hours, then cooled cooling, water was added dropwise to the system, and then liquid separation, the organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to give a yellow solid which was recrystallized from dichloromethane and methanol to give (R) -1- ferrocenyl ethyl-di-tert-butylphosphine 347g yield 97%, ee value of 99.5%.
  • 53
  • [ 1271-51-8 ]
  • [ 829-84-5 ]
  • (R)-1-ferrocenylethyldicyclohexylphosphine [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With 2,6-bis(3,5-dimethylphenyl)-4-hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide In toluene at 100℃; for 10h; Inert atmosphere; 2.1 Example 2(1) (R) -1- ferrocenyl ethyl dicyclohexylphosphino Synthesis Under argon, into a dried reactor were added successively vinyl ferrocene (1mol, 212g), (R ) -3,3'-bis (3,5-dimethylphenyl) -1,1 ' - binaphthol phosphonate (0.1mol, 55g) and 1L of toluene was added dicyclohexyl phosphine (1mol, 198g), was heated to 100 deg.] C for 10 hours, then cooled cooling, water was added dropwise to the system, and then liquid separation The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to give a yellow solid which was recrystallized from dichloromethane and methanol to give (R) -1- ferrocenyl ethyl dicyclohexylphosphino 394 g, yield 96%, ee value of 99.4%.
  • 54
  • [ 1271-51-8 ]
  • [ 153747-97-8 ]
  • tert-butyl (R)-4-(5-(1-ferrocenylethyl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]
  • 55
  • [ 326474-67-3 ]
  • [ 1271-51-8 ]
  • (R)-3-(1-ferrocenylethyl)-1-methyl-1H-indazole [ No CAS ]
  • 56
  • [ 1271-51-8 ]
  • [ 54-42-2 ]
  • 5-ferrocenylethenyl-2'-deoxyuridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With palladium diacetate; triphenylphosphine In acetonitrile at 60℃; for 48h; Alkaline conditions; 5-Iodo-2'-deoxyuridine was allowed to react at 60 °C for 48 h under basic conditions in CH3CN with vinylferrocene (1.2 equiv.) in the presence of palladium acetate (0.01 equiv.) and triphenylphosphine (0.02 equiv.), which afforded the coupling product 1 in 43% yield.
  • 57
  • [ 1271-51-8 ]
  • 2-(2,6-bis((E)-4-bromostyryl)-4H-pyran-4-ylidene)-1H-indene-1,3(2H)dione [ No CAS ]
  • 2-{2,6-bis[4-(2-ferrocenylvinyl)styryl]-4H-pyran-4-ylidine}1,3-indandione [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With tetrabutylammonium tetrafluoroborate; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 80℃; Inert atmosphere; General procedure for the Palladium-Catalyzed coupling ofvinylferrocene A mixture of vinylferrocene (1 mmol), K2CO3 (2.5or 5 mmol), tetrabutylammonium tetrafluoroborat (2.5 or 5 mmol),the given amount of appropriate bromine-substituted compoundand catalytic amount of Pd(OAC)2 in 10 ml DMF was stirred at 80 °Cunder argon atmosphere overnight. After the completion of thereaction, the cooled mixture was filtered, diluted with CH2Cl2(50 ml) and washed with H2O (3 x 50 ml). The organic phase was dried over Na2SO4, filtered and the solvent was removed under thereduce pressure. The crude products were purified by columnchromatography on silica gel with hexane/EtOAC as eluent. Specificdetails for each compound are given below.
  • 58
  • [ 1271-51-8 ]
  • 2,6-bis-[(4-bromophenyl)vinyl]-4H-pyran-4-one [ No CAS ]
  • 2,6-bis[4-(2-ferrocenylvinyl)styryl]-4H-pyran-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With tetrabutylammonium tetrafluoroborate; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 80℃; Inert atmosphere; General procedure for the Palladium-Catalyzed coupling ofvinylferrocene A mixture of vinylferrocene (1 mmol), K2CO3 (2.5or 5 mmol), tetrabutylammonium tetrafluoroborat (2.5 or 5 mmol),the given amount of appropriate bromine-substituted compoundand catalytic amount of Pd(OAC)2 in 10 ml DMF was stirred at 80 °Cunder argon atmosphere overnight. After the completion of thereaction, the cooled mixture was filtered, diluted with CH2Cl2(50 ml) and washed with H2O (3 x 50 ml). The organic phase was dried over Na2SO4, filtered and the solvent was removed under thereduce pressure. The crude products were purified by columnchromatography on silica gel with hexane/EtOAC as eluent. Specificdetails for each compound are given below.
  • 59
  • [ 28286-88-6 ]
  • [ 1271-51-8 ]
  • 2-{2,6-bis[4-(2-ferrocenylvinyl)styryl]-4H-pyran-4-ylidine}malononitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With piperidine In acetonitrile for 1h; Reflux; Inert atmosphere; Condensation of 4-(2-ferrocenylvinyl)benzaldehyde withpyran derivatives A solution of 4H-pyrane derivative (4, 7a and7b) (1 mmol), 4-(2-ferrocenylvinyl)benzaldehyde (2 mmol) andpiperidine (1 mL) in dry acetonitrile (10 mL) was refluxed for 1 hunder argon atmosphere. The reaction was controlled with TLCmethod by monitoring the 4-(2-ferrocenylvinyl) benzaldehyde inthe solution of reaction. After the completion of the reaction, thesolution was cooled to room temperature and the product waspurified using column chromatography over silica gel and hexane/EtOAC as eluent. Further purification was performed by recrystallizationfrom hexane and EtOAc to give corresponding compoundas a pure solid. Specific details for each compound are given belowand spectral data in each case is similar to reported one in above.2,6-Bis [4-(2-ferrocenylvinyl)styryl]-4H-pyran-4-one (6):from 0.1 g (0.32 mmol) 4-(2-Ferrocenylvinyl) benzaldehyde and0.02 g (0.11 mmol) 2, 6-Methyl-4H-pyran-4-one, 0.08 g (0.13 mmol)orange solid was obtained in 75% yield.
  • 60
  • [ 71107-31-8 ]
  • [ 1271-51-8 ]
  • 2-{2,6-bis[4-(2-ferrocenylvinyl)styryl]-4H-pyran-4-ylidine}1,3-indandione [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With piperidine In acetonitrile for 1h; Reflux; Inert atmosphere; Condensation of 4-(2-ferrocenylvinyl)benzaldehyde withpyran derivatives A solution of 4H-pyrane derivative (4, 7a and7b) (1 mmol), 4-(2-ferrocenylvinyl)benzaldehyde (2 mmol) andpiperidine (1 mL) in dry acetonitrile (10 mL) was refluxed for 1 hunder argon atmosphere. The reaction was controlled with TLCmethod by monitoring the 4-(2-ferrocenylvinyl) benzaldehyde inthe solution of reaction. After the completion of the reaction, thesolution was cooled to room temperature and the product waspurified using column chromatography over silica gel and hexane/EtOAC as eluent. Further purification was performed by recrystallizationfrom hexane and EtOAc to give corresponding compoundas a pure solid. Specific details for each compound are given belowand spectral data in each case is similar to reported one in above.2,6-Bis [4-(2-ferrocenylvinyl)styryl]-4H-pyran-4-one (6):from 0.1 g (0.32 mmol) 4-(2-Ferrocenylvinyl) benzaldehyde and0.02 g (0.11 mmol) 2, 6-Methyl-4H-pyran-4-one, 0.08 g (0.13 mmol)orange solid was obtained in 75% yield.
  • 61
  • [ 1271-51-8 ]
  • 2-{2,6-bis-[(4-bromophenyl)vinyl]-4H-pyran-4-ylidene}malononitrile [ No CAS ]
  • 2-{2,6-bis[4-(2-ferrocenylvinyl)styryl]-4H-pyran-4-ylidine}malononitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With tetrabutylammonium tetrafluoroborate; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 80℃; Inert atmosphere; General procedure for the Palladium-Catalyzed coupling ofvinylferrocene A mixture of vinylferrocene (1 mmol), K2CO3 (2.5or 5 mmol), tetrabutylammonium tetrafluoroborat (2.5 or 5 mmol),the given amount of appropriate bromine-substituted compoundand catalytic amount of Pd(OAC)2 in 10 ml DMF was stirred at 80 °Cunder argon atmosphere overnight. After the completion of thereaction, the cooled mixture was filtered, diluted with CH2Cl2(50 ml) and washed with H2O (3 x 50 ml). The organic phase was dried over Na2SO4, filtered and the solvent was removed under thereduce pressure. The crude products were purified by columnchromatography on silica gel with hexane/EtOAC as eluent. Specificdetails for each compound are given below.
  • 62
  • [ 1271-51-8 ]
  • C12H12FeN6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With sodium azide; manganese(II) bromide tetrahydrate; lithium perchlorate; acetic acid In acetonitrile at 22℃; Electrochemical reaction; Inert atmosphere; Green chemistry; chemoselective reaction;
  • 63
  • [ 1271-51-8 ]
  • [ 52742-32-2 ]
  • 1-ethylferrocene [ No CAS ]
  • butane-2,3-diyldiferrocene [ No CAS ]
  • (S)-N,N-dibenzyl-1-(ferrocenyl)ethan-1-amine [ No CAS ]
  • (R)-N,N-dibenzyl-1-(ferrocenyl)ethan-1-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 20 % ee 2: 15% 3: 20% With (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; (dimethoxy)methylsilane; copper diacetate In tetrahydrofuran at 20 - 40℃; Schlenk technique; Procedure for Enantiomerically Enriched N,N-Dibenzyl-1-(ferro-cenyl)ethan-1-amine [(S)-8] In anhydrous THF (1 mL) was dissolved 6 mol% Cu(OAc) 2 (10.9 mg,0.066 mmol) and 6.6 mol% of ligand (R)-DTBM-SEGPHOS (78 mg,0.060 mmol). The mixture was stirred for 15 min at r.t., then DMMS(0.5 mL, 4 equiv, 4 mmol) was added dropwise and stirring was con-tinued for 10 min at the same temperature. The solution of amine 7(381 mg, 1.2 mmol) and vinylferrocene 4 (212 mg, 1 mmol) was thenadded by using Schlenk techniques to the tube containing the solu-tion of [L*CuH] complex. The reaction mixture was stirred at 40 °Covernight, then the mixture was diluted with EtOAc (5 mL) and 5%solution of Na 2 CO 3 (5 mL) was added dropwise. The solution was ex-tracted with EtOAc (3 × 25 mL), the collected organic layers werewashed with brine (25 mL), dried over Na 2 SO 4 , filtrated, and the sol-vent was removed under reduced pressure to afford the crude prod-uct. The crude product was purified by chromatography on SiO 2 (hex-anes/EtOAc, 30:1 + 1% Et 3 N; R f = 0.4) to afford target product 8.Yield: 68 mg (18%); orange solid; mp 62-65 °C; [α] D20 -14.5 (c 1.00,CHCl 3 ); HPLC analysis (Chiralcel OD-H; hexane/ i PrOH, 99:1; 0.8mL/min; 254 nm) indicated 20% ee: t R = 5.9 (major), 6.5 (minor) min.IR (ATR): 1234, 1103, 1068, 1022, 998, 822, 749, 728, 697, 514, 487cm -1 .1 H NMR (600 MHz, CDCl 3 ): δ = 7.39 (d, J = 7.4 Hz, 4 H, -Ph), 7.31 (t, J =7.6 Hz, 4 H, -Ph), 7.23 (t, J = 7.3 Hz, 2 H, -Ph), 4.27-4.27 (m, 1 H, Fc),4.18-4.14 (m, 3 H, Fc), 4.02 (s, 5 H, Cp Fc ), 3.81 (q, J = 6.9 Hz, 1 H, H α ),3.53 (d, J = 14.1 Hz, 2 H, CH 2 -Ph), 3.36 (d, J = 14.1 Hz, 2 H, -CH 2 -Ph),1.47 (d, J = 6.9 Hz, 3 H, -CH 3 ).13 C NMR (151 MHz, CDCl 3 ): δ = 140.9 (2×C, Cq Ph ), 128.6 (4×C, -Ph),128.2 (4×C, -Ph), 126.7 (2×C, -Ph), 88.9 (Cq Fc ), 69.1 (-CH Fc ), 68.7 (5×C,Cp Fc ), 67.6 (-CH Fc ), 67.1 (-CH Fc ), 66.9 (-CH Fc ), 52.3 (2×C, -CH 2 -Ph), 52.2(-CH α ), 15.4 (-CH 3 ).HRMS (ESI): m/z calcd for [M + H + ] C 26 H 28 FeN + : 410.1571; found:410.1565.
  • 64
  • [ 1271-51-8 ]
  • [ 609-73-4 ]
  • 1-ferrocenyl-2-(ortho-nitrophenyl)ethylene [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With potassium phosphate; C24H18FeN4; tetrabutylammomium bromide; palladium diacetate In water at 40℃; for 3h; 4 General procedure: 25mL reaction flask, weighing 2mol% palladium acetate and 4mol% ferrocenylpyrimidine multidentate ligand 6h, adding 12 water, stirring for 5min, 4 mmol of p-nitrochlorobenzene, 4.8 mmol of butyl acrylate, 6 mmol of potassium phosphate, and 0.8 mmol of tetrabutylammonium bromide were added successively. The reaction was heated to 80°C until the reaction was complete (the reaction did not continue after about 6 h, and palladium black appeared in the reaction flask). After adding 25 mL of ethyl acetate and washing three times with water, the organic phases were combined, dried over anhydrous sodium sulfate, concentrated, and the residue was separated by column chromatography. PE/EA=12:1 was used as an eluent to obtain 707 mg of a yellow solid with a yield of 71%.
  • 65
  • [ 1271-51-8 ]
  • [ 19193-93-2 ]
  • C57H45Fe3N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
49.5% With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In tetrahydrofuran Inert atmosphere; Schlenk technique; Reflux; 4.2. General procedure for compounds 1 and 3 General procedure: In an Schlenk tube under argon one of the following central coresC1, or C2 was mixed with 5% palladium (II) acetate, Pd(OAc)2, 10%Tris(o-tolyl)phosphine, P(o-tol)3, and vinyl ferrocene, 1-Fc, in triethylamine/THF, 15 mL/15 mL. The resulting mixture was stirred and refluxedovernight. After removing the solvent under reduced pressure,the oil obtained was washed with distillated water and extracted inCH2Cl2 three times and dried over MgSO4. The extract was concentratedto dryness and purified by column chromatography (silica gel60) using hexane/CH2Cl2 2:1 (V/V) mixtures as eluent. The correspondingcompounds were isolated after removing the solvent in a rotaryevaporator. Compound 1. 1-Fc (187 mg, 8.84 mmol), C1 (150 mg,0.253 mmol), Pd(OAc)2 (2.8 mg, 0.0126 mmol), P(o-tol)3 (7.7 mg,0.0253 mmol), triethylamine/THF, 15 mL/15 mL. Yield 49.5%. IR wavenumber(KBr): =1713 cm-1 (eC]O), 1590 cm-1 (eC]Ce). 1HNMR (CDCl3, 400 MHz): δ=4.10 (15H, pst, C5H5), 4.27 (6H,pst-C5H4), 4.44 (6H, s, -C5H4), 6.68 (3H, d, J=16.0 Hz, ]CH), 6.89(3H, d, J=16.0 Hz, ]CH), 7.31 (6H, d, J=8.2 Hz, Harom), 7.50 (6H, d,J=8.4 Hz, Harom). 13C NMR (100.6 MHz, CDCl3): δ=67.05, 69.25,69.66, 82.76, 124.74, 126.48, 128.53, 128.60, 128.91, 131.70, 139.04.Analysis calculated for C57H45O3Fe3N3: C, 69.3; H, 4.59; N, 4.26.Found: C, 68.61; H, 4.12; N, 4.32. MP: 199 °C - 200 °C.
  • 66
  • [ 1271-51-8 ]
  • [ 1019209-38-1 ]
  • C66H48Fe3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
51.2% With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In tetrahydrofuran Inert atmosphere; Schlenk technique; Reflux; 4.2. General procedure for compounds 1 and 3 General procedure: In an Schlenk tube under argon one of the following central coresC1, or C2 was mixed with 5% palladium (II) acetate, Pd(OAc)2, 10%Tris(o-tolyl)phosphine, P(o-tol)3, and vinyl ferrocene, 1-Fc, in triethylamine/THF, 15 mL/15 mL. The resulting mixture was stirred and refluxedovernight. After removing the solvent under reduced pressure,the oil obtained was washed with distillated water and extracted inCH2Cl2 three times and dried over MgSO4. The extract was concentratedto dryness and purified by column chromatography (silica gel60) using hexane/CH2Cl2 2:1 (V/V) mixtures as eluent. The correspondingcompounds were isolated after removing the solvent in a rotaryevaporator.
  • 67
  • [ 1271-51-8 ]
  • [ 353-83-3 ]
  • [ 86-74-8 ]
  • 9-(4,4,4-trifluoro-1-ferrocene-butyl)-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With copper(l) chloride; lithium tert-butoxide In acetonitrile at 20℃; for 60h; Glovebox; Inert atmosphere; Irradiation; Green chemistry;
  • 68
  • [ 1271-51-8 ]
  • [ 86-74-8 ]
  • 9-(1-ferrocenylethyl)-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% Stage #1: 9H-carbazole With copper(II) bis(trifluoromethanesulfonate); lithium tert-butoxide In acetonitrile at 20℃; for 0.0833333 - 0.166667h; Inert atmosphere; Stage #2: vinyl ferrocene In acetonitrile at 20℃; for 48h; Inert atmosphere; Irradiation; regioselective reaction;
  • 69
  • [ 1271-51-8 ]
  • [ 25015-63-8 ]
  • ferrocene vinyl boronic acid pinacol ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With bis(cyclopentadienyl)dihydrozirconium In toluene at 25℃; Inert atmosphere; 33 Example 32 Synthesis method of an alkenyl borate compound: Add 1t (0.2 mmol, 42mg) of vinyl ferrocene, 2a (0.2 mmol, 29 μL), toluene (1 mL), and Cp to the reaction tube in this order.2ZrH2(0.01 mmol, 2.3 mg). Stir the reaction at room temperature under a nitrogen (1 atm) atmosphere.GC detection until the reaction is complete.Filter through celite, spin dry the solvent under reduced pressure, and purify the residue by silica gel column chromatography. Use petroleum ether: ethyl acetate (40 mL: 1 mL) as the eluent to obtain ferrocene vinyl boric acid as a yellow oil Pinacol ester 3t (63mg, 80%).
  • 70
  • [ 1271-51-8 ]
  • [ 99-99-0 ]
  • [ 727651-97-0 ]
YieldReaction ConditionsOperation in experiment
57% With Triethoxysilane; C25H22FeNPS In tetrahydrofuran at 40℃; for 24h;
  • 71
  • [ 1271-51-8 ]
  • [ 137156-30-0 ]
  • (S,E)-5-cyclohexyl-2-ferrocenylpent-4-en-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% Stage #1: vinyl ferrocene; Phosphoric acid 1-cyclohexyl-allyl ester diethyl ester With (R,R)-1,2-bis[tert-butyl(methyl)phosphino]benzene; lithium methanolate; bis(pinacol)diborane; copper(l) chloride In N,N-dimethyl acetamide at 40℃; for 12h; Schlenk technique; Inert atmosphere; Stage #2: With sodium perborate tetrahydrate In tetrahydrofuran; water at 20℃; for 5h; enantioselective reaction;
  • 72
  • [ 1271-51-8 ]
  • C9H7F5N2O2S [ No CAS ]
  • C14H14FeO [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With meso-tetraphenylporphyrin iron(III) chloride; sodium hydroxide In water; toluene at 60℃; for 22h; Inert atmosphere; diastereoselective reaction;
  • 73
  • [ 1271-51-8 ]
  • C9H7F5N2O2S [ No CAS ]
  • (trans-2-(drifluoromethyl)cyclopropyl)ferrocene [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With meso-tetraphenylporphyrin iron(III) chloride; potassium carbonate In 1,4-dioxane at 40℃; for 22h; Sealed tube; Inert atmosphere; diastereoselective reaction;
  • 74
  • 1-(vinyloxy)ethylferrocene [ No CAS ]
  • [ 1271-51-8 ]
  • 3-ferrocenylbutanal [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 27% 2: 25% In neat (no solvent) at 120 - 160℃; for 2.5h; 2.1. Thermal Rearrangement of Vinyloxyalkylferrocene 1b Vinyl ether 1b (256 mg, 1 mmol) in a dry solvent (1 mL) or neat was stirred at 120-160 °C the corresponding time (1-2.5 h). Upon completion, the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on neutral alumina (4 cmlayer, eluent: hexane-Et2O, 1:0→1:1) to afford the desired aldehyde 3b and vinylferrocene (4) as a by-product.
  • 75
  • [ 1271-51-8 ]
  • [ 25015-63-8 ]
  • 2,2'-(2-ferrocenylethane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% With zirconocene dichloride; lithium methanolate In toluene at 100℃; for 8h; Inert atmosphere; 52 Example 52 A method for preparing gem-diboron compounds by selective 1,1-diboration of olefins: Add Cp2ZrCl2 (0.01 mmol, 2.9 mg) to the reaction tube in sequence,MeOLi (0.2 mmol, 7.6 mg), toluene (1 mL), pinacol borane 2a (0.6 mmol, 87 μL), vinyl ferrocene 1y (0.2 mmol, 42 mg), The reaction was stirred at 100 °C for 8 h under a nitrogen (1 atm) atmosphere. GC-MS detection reaction is completed. Add 3 mL of methanol at room temperature, then spin-dry the solvent under reduced pressure, and purify the product by silica gel column chromatography.Using petroleum ether: ethyl acetate (15 mL: 1 mL) as eluent,1,1-[bis(pinacol borate)]-ethyl ferrocene is obtained as a yellow solid3y (28 mg, 35%).
35% With zirconocene dichloride; lithium methanolate In toluene at 100℃; Inert atmosphere;
  • 76
  • [ 1271-51-8 ]
  • d<SUB>3</SUB>-vinylferrocene [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With tetrakis(triphenylphosphine) palladium(0); (S)-Mandelic acid; water-d2; tricyclohexylphosphine In toluene at 120℃; for 16h; Inert atmosphere; Catalytic Deuteration of Styrenes; General Procedure General procedure: In a glass tube, alkene 1 (0.20 mmol), Pd(PPh3)4 (0.01 mmol), PCy3 (0.02 mmol) and (+)-mandelic acid (0.06 mmol) were added sequentially and the tube was then purged with nitrogen three times. Subsequently, toluene (2.0 mL, 0.1 M) and D2O (10 mmol) were added under a N2 atmosphere and the tube was placed in a pre-heated oil bath at 120 °C and the contents stirred overnight (16 h). The reaction mixture was then cooled to room temperature and diluted with CH2Cl2 (10 mL). The mixture was directly concentrated under reduced pressure and the crude residue was purified by chromatography on silica gel.
  • 77
  • [ 75-91-2 ]
  • [ 1271-51-8 ]
  • [ 1271-55-2 ]
YieldReaction ConditionsOperation in experiment
95% With C21H19N5Pd(2+)*2BF4(1-) In decane; acetonitrile at 45℃; for 12h;
  • 78
  • [ 1271-51-8 ]
  • Mo(N-2,6-Me<SUB>2</SUB>-C<SUB>6</SUB>H<SUB>3</SUB>)(1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene)(CHCMe<SUB>2</SUB>Ph)(OTf)<SUB>2</SUB> [ No CAS ]
  • C42H45F6FeMoN3O6S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% In dichloromethane at 20℃;
  • 79
  • [ 1271-51-8 ]
  • Mo(N-2,6-Me<SUB>2</SUB>-C<SUB>6</SUB>H<SUB>3</SUB>)(IMes)(CHCMe<SUB>2</SUB>Ph)(OTf)<SUB>2 </SUB> [ No CAS ]
  • [Mo(N-2,6-Me2-C6H3)(1,3-dimesitylimidazol-2-ylidene)(CHFc)(OTf)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% In dichloromethane at 20℃;
  • 80
  • [ 617-86-7 ]
  • [ 1271-51-8 ]
  • (E)-(C5H5)(C5H4)FeCHCHSi(C2H5)3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With dimanganese decacarbonyl; N,N-bis(diphenylphosphino)isopropylamine at 140℃; for 24h; Sealed tube; General procedure for the dehydrosilylation reaction of non-gaseous alkenes General procedure: To an oven-dried 10-ml sealed tube, [Mn2(CO)10] (5 mol%), iPrPNP ligand (L12; 10 mol%, 0.1 mmol) and PhCF3 (0.2 ml) were added under air conditions and the mixture was stirred at 80 °C for 50 min to 1 h to become a deeply red homogeneous solution. Alkene (1.0 mmol) and silane (1.0 mmol) were then rapidly added, successively, into the sealed tubes with a liquid-transferring gun. The resulting yellow reaction mixture was rigorously stirred at 140 °C for 24 h. Once the reaction was finished, the solvent was removed under vacuum and the resulting residue was purified by column chromatography on silica gel to afford the products.
  • 81
  • [ 1271-51-8 ]
  • [ 1666-13-3 ]
  • [ 7732-18-5 ]
  • 1-ferroceneyl-2-(phenylselanyl)ethan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With air In acetonitrile at 20℃; for 20h; Irradiation; 6 Example 6 At room temperature, a 10 ml round bottom flask equipped with a magnetic stirrer was charged with 2-vinylferrocene (0.5 mmol), diphenyldiselenide (0.25 mmol), and a mixed solvent of acetonitrile/water ( 1/1, 2ml), after the addition, place a 23-watt white compact fluorescent lamp at a distance of 1 cm from the round-bottom flask, and react at room temperature for 20 hours under open conditions.After the completion of the reaction, the reaction solution was poured into 10 mL water, extracted three times with ethyl acetate, the organic layers were combined, dried over anhydrous sodium sulfate, filtered, the organic phase was removed from the solvent by a rotary evaporator, and the residue was purified with a silica gel column (silica gel The specification is 200-300 mesh, the eluent is petroleum ether/ethyl acetate = 10:1), 173 mg of colorless oily liquid is obtained, and the yield is 90%.
  • 82
  • [ 1271-51-8 ]
  • [ 1576-37-0 ]
  • 4-methyl-N-(1-phenyl-3-(ferrocenyl)propyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With bis(1,5-cyclooctadiene)nickel (0); potassium <i>tert</i>-butylate; tricyclohexylphosphine; phenylboronic acid In toluene at 120℃; for 20h; Inert atmosphere; 32 Preparation of 4-Methyl-N-(1-phenyl-3-(ferrocenyl)propyl)benzenesulfonamide In a nitrogen atmosphere, add raw material 1a (0.2mmol, 52.2mg), raw material 2i (0.4mmol, 84.8mg), KOtBu (0.05mmol, 5.6mg), PhB(OH)2 (0.05mmol, 6.1 mg), Ni(cod)2(0.005mmol, 1.4mg), and PCy3(0.01mmol, 2.8mg), finally add Toluene(0.3mL), stir at 120 for 20 hours, cool to room temperature, concentrate, and directly column The target product 4i was obtained by chromatographic separation with a yield of 91% and 86.2 mg.
  • 83
  • [ 1271-51-8 ]
  • [ 5455-59-4 ]
  • C18H18FeN2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With (R)-3,3'-bis(9-anthracenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In chlorobenzene at 20℃; for 24h; Molecular sieve; enantioselective reaction;
  • 84
  • 1-methoxyethyl ferrocene [ No CAS ]
  • [ 5455-59-4 ]
  • [ 1271-51-8 ]
  • C18H18FeN2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 47% 2: 43% With (R)-3,3'-bis(9-anthracenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In toluene at 20℃; for 2h; Molecular sieve; enantioselective reaction;
  • 85
  • [ 1271-51-8 ]
  • [ 3481-02-5 ]
  • 2- ferrocenylcyclopentyl(phenyl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: vinyl ferrocene; phenyl cyclopropyl ketone With bis((-)pinanediolato)diboron; 3-pentyl isonicotinate; methoxybenzene at 100℃; for 12h; Inert atmosphere; Schlenk technique; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol at 80℃; for 3h; Inert atmosphere; Schlenk technique; diastereoselective reaction;
Same Skeleton Products
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